Sales Enablement Specialist


The Sales Enablement Specialists (SES) represent the InsideOut brand and our core ideology, which is the design, build, and install of Sales Plays for our clients. Sales Enablement Specialists are on the front line with our clients, conducting Workshops to design and build Sales Plays custom to each client. An SES directs senior level decision-makers at enterprise companies through the InsideOut Play Process.

An SES is adaptable and can manage the client’s expectations and address questions throughout the process. This role requires knowledge of the inside sales industry and the ability to conceptualize how similar sales plays can be applied across a variety of different industries, buyer personas, and products.

We define a Sales Play as the strategic sales motion for sales teams to engage with buyers and potential prospects in a live setting. Sales Plays also take into consideration at what time a message is sent, the content of that message, what type of medium to use (email, social, phone, video, etc.) to ensure optimum efficiency.

About the Company:

InsideOut is a Sales Innovation Lab designed to assist high growth companies with sales optimization through the creation, testing, measurement, and implementation of certified sales plays. Our Sales Innovation Lab is redefining the inside sales industry by allowing leaders to determine and validate the highest converting plays to acquire, grow, and retain their customer base. Our teams are comprised of results-oriented, growth focused, and innovative individuals who embrace high activity, creativity, and change.

Employee Benefits:

  • Health insurance premiums paid 100% by the company
  • 401(k) with 4% company match
  • Life insurance premium paid 100% by the company
  • 15 paid personal days off (vacation/sick)
  • 8.5 paid Holidays off
  • Ability to work with some of the world’s most advanced companies, acquiring a deep understanding of their sales processes, techniques, teams, and technologies
  • Professional development and sales skill mastery through internal and external training opportunities
  • The opportunity to join a fast-growing organization and experience rapid career growth

Duties and Responsibilities:

  • Attend and/or lead Kick-Off meetings and scoping sessions
  • Participate and/or lead coordination of workshops
  • Lead the customer stakeholders through the workshopping process end to end
  • Conduct benchmark analysis
  • Gather current KPIs and statistics to establish criteria for success
  • Conduct health checks on customer’s existing Sales Plays
  • Review, understand, interpret, and communicate findings
  • Collaborate with customer stakeholders on identification & prioritization of new Sales Plays
  • Create and publish a Sales Play campaign calendar to the customer
  • Manage end-to-end process of creating the Sales Play
  • Collate content with client’s assistance for creation
  • Assist Content Designer in messaging review and/or creation
  • Work directly with the Content and Design Specialist to ensure that the Sales Plays meet the customer expectations and clearly represent the strategy discovered via the workshop
  • Review Sales Plays with internal and external stakeholders to ensure alignment
  • Adhere and manage the Sales Play campaign calendar with the customer and continue to update internal and external stakeholders based on client’s needs and requirements
  • Communicate outcomes from workshop to internal teams at InsideOut
  • Provide Sales Play training to end users prior to Sales Play Go Live
  • Collaborate with internal sales team during standard rhythm of business to identify opportunities for up-sell/cross-sell
  • Balance one-time projects and ongoing monthly projects to manage customers through the process in order to achieve end deliverable(s)
  • Work directly with the internal Account Executive/s to plan for upcoming new projects
  • Ability to travel domestically and internationally is required, with travel time up to 40%; when not traveling, the SES will work from our St. Petersburg office primarily

*The duties, responsibilities, and conditions described are not necessarily a comprehensive list. Additional tasks and requirements may be assigned to the employee from time to time, as necessitated by business demands. Given the nature of the business, the company retains the right to modify the essential functions of this position at any time.


Skills and Experience You Possess:

  • 3+ years in sales or sales consulting with significant knowledge of sales organizational structures, processes, and selling techniques
  • Proven presentation skills both in person and in virtual meetings and workshops
  • Demonstrate excellence in verbal and written communication skills
  • Demonstrate the ability to converse and engage with customer stakeholders, from end user to executive
  • Ability to build and maintain long term relationships with customers
  • Able to quickly understand and assess strategy
  • Ability to work well under pressure and adhere to strict deadlines
  • Must exude confidence and clarity in communication
  • Project Management experience is a plus
  • Advanced level expertise in Microsoft Office Suite (PowerPoint, Excel, Word)
  • Strong analytical, written, and verbal skills
  • Experience in Adobe Photoshop, InDesign, and Illustrator is a plus
  • Experience with sales tech stack such as sales engagement tools, CRMs, chat platforms, video emails, and marketing automation tools, etc. is a HUGE plus

Offer Contingencies:

This role is contingent upon passing both a background check and a drug screening prior to employment (post-offer)

  • Employer check
  • Qualifications check
  • Right to work in the USA

Job Category: Play Ops
Job Type: Full Time
Job Location: St. Petersburg - Florida

Apply for this position

Allowed Type(s): .pdf, .doc, .docx